Sulfuric Acid → 1,2,3,4-Benzenetetrol

Participants

Reaction Conditions

Reaction Steps

A solution of myo-2-inosose (11.0 g, 61.2 mmol) in 310 mL of degassed 0.5 M H2SO4 was refluxed under Ar. After 9 h, the solution was cooled to 4° C. and then adjusted to pH 4 by addition of saturated aqueous NaHCO3. Concentration of the reaction solution to 100 mL was followed by continuous liquid-liquid extraction for 18 h using t-butyl methyl ether (500 mL). Upon concentration of the organic layer to 100 mL, a precipitate formed which was filtered, washed with cold hexanes, and dried to afford 1 (4.72 g, 54%) as a tan powder. Addition of hexanes (300 mL) to the filtrate followed by filtering, washing, and drying of the resulting precipitate afforded additional 1 (1.08 g, 12%). mp 162-164° C. 1H NMR (d6-acetone): δ7.24 (s, 4 H), 6.20 (s, 2 H). 13C NMR (d6-acetone): δ139.7, 134.7, 106.2. Anal. Calcd for C6H6O4: C, 50.71; H, 4.23. Found: C, 50.63; H, 4.32. HRMS (FAB) calcd for C6H6O4 (M+H+): 142.0266. Found: 142.0268.

Provenance & Evidence